#------------------------------------------------------------------------------
#$Date: 2025-03-04 20:12:46 +0200 (Tue, 04 Mar 2025) $
#$Revision: 297999 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/40/7134078.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7134078
loop_
_publ_author_name
'Maurya, Naveen Kumar'
'Singh, Anushka'
'Sahu, Ankita'
'Kumar, Asit'
'Kant, Ruchir'
'Rao, Vishal Govind'
'Shukla, Sanjeev K.'
'Kuram, Malleswara Rao'
_publ_section_title
;
 Suzuki-Miyaura/Mizoroki-Heck coupling cascade to access
 2,2'-bifunctionalized biaryls.
;
_journal_issue                   8
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1673
_journal_page_last               1676
_journal_paper_doi               10.1039/d4cc05763e
_journal_volume                  61
_journal_year                    2025
_chemical_formula_sum            'C23 H19 Cl O2'
_chemical_formula_weight         362.83
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2024-01-24 deposited with the CCDC.	2024-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                102.5890(10)
_cell_angle_beta                 97.7710(10)
_cell_angle_gamma                108.9250(10)
_cell_formula_units_Z            2
_cell_length_a                   7.87220(10)
_cell_length_b                   11.3433(2)
_cell_length_c                   11.65270(10)
_cell_measurement_reflns_used    7596
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.9960
_cell_measurement_theta_min      3.9850
_cell_volume                     936.44(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11487
_diffrn_reflns_theta_full        77.75
_diffrn_reflns_theta_max         77.75
_diffrn_reflns_theta_min         3.99
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.907
_exptl_absorpt_correction_T_max  0.7630
_exptl_absorpt_correction_T_min  0.6791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0070(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0529P)²+0.1743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1105
_reflns_number_gt                3369
_reflns_number_total             3763
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4cc05763e2.cif
_cod_data_source_block           xxx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_refine_ls_hydrogen_treatment' value 'Constr' was changed
to 'constr' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7134078.cif.
;
_cod_database_code               7134078
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.59068(18) 0.28148(13) 0.06085(11) 0.0404(3) Uani 1 1 d . . .
C2 C 0.5103(2) 0.30371(14) -0.04284(13) 0.0479(3) Uani 1 1 d . . .
H2 H 0.5819 0.3659 -0.0747 0.057 Uiso 1 1 calc R . .
C3 C 0.3273(2) 0.23570(16) -0.09914(13) 0.0532(4) Uani 1 1 d . . .
H3 H 0.2763 0.2525 -0.1676 0.064 Uiso 1 1 calc R . .
C4 C 0.2210(2) 0.14281(17) -0.05328(14) 0.0575(4) Uani 1 1 d . . .
H4 H 0.0979 0.0958 -0.0913 0.069 Uiso 1 1 calc R . .
C5 C 0.2969(2) 0.11944(15) 0.04900(13) 0.0513(4) Uani 1 1 d . . .
H5 H 0.2239 0.0558 0.0787 0.062 Uiso 1 1 calc R . .
C6 C 0.48048(18) 0.18867(13) 0.10922(11) 0.0406(3) Uani 1 1 d . . .
C7 C 0.79052(18) 0.35592(13) 0.11521(11) 0.0409(3) Uani 1 1 d . . .
C8 C 0.86036(19) 0.49023(14) 0.13652(13) 0.0454(3) Uani 1 1 d . . .
H8 H 0.7832 0.5331 0.1163 0.054 Uiso 1 1 calc R . .
C9 C 1.0450(2) 0.55921(14) 0.18790(13) 0.0489(3) Uani 1 1 d . . .
C10 C 1.1643(2) 0.49934(17) 0.21739(14) 0.0550(4) Uani 1 1 d . . .
H10 H 1.2884 0.5474 0.2518 0.066 Uiso 1 1 calc R . .
C11 C 1.0950(2) 0.36566(18) 0.19444(17) 0.0602(4) Uani 1 1 d . . .
H11 H 1.1735 0.3232 0.2133 0.072 Uiso 1 1 calc R . .
C12 C 0.9106(2) 0.29454(15) 0.14384(14) 0.0515(4) Uani 1 1 d . . .
H12 H 0.8664 0.2048 0.1288 0.062 Uiso 1 1 calc R . .
C14 C 0.54675(18) 0.16171(13) 0.22336(12) 0.0408(3) Uani 1 1 d . . .
C15 C 0.5323(2) 0.03550(14) 0.22102(13) 0.0489(3) Uani 1 1 d . . .
H15 H 0.4854 -0.0292 0.1481 0.059 Uiso 1 1 calc R . .
C16 C 0.5860(2) 0.00418(15) 0.32449(15) 0.0544(4) Uani 1 1 d . . .
H16 H 0.5736 -0.0810 0.3211 0.065 Uiso 1 1 calc R . .
C17 C 0.6583(2) 0.09977(16) 0.43320(14) 0.0555(4) Uani 1 1 d . . .
H17 H 0.6969 0.0795 0.5029 0.067 Uiso 1 1 calc R . .
C18 C 0.6729(2) 0.22518(15) 0.43805(13) 0.0509(4) Uani 1 1 d . . .
H18 H 0.7215 0.2888 0.5116 0.061 Uiso 1 1 calc R . .
C19 C 0.61643(19) 0.25909(13) 0.33495(12) 0.0421(3) Uani 1 1 d . . .
C20 C 0.6227(2) 0.39105(13) 0.34304(12) 0.0435(3) Uani 1 1 d . . .
H20 H 0.5549 0.4021 0.2772 0.052 Uiso 1 1 calc R . .
C21 C 0.7144(2) 0.49628(14) 0.43379(13) 0.0531(4) Uani 1 1 d . . .
H21 H 0.7832 0.4899 0.5020 0.064 Uiso 1 1 calc R . .
C22 C 0.7088(2) 0.62297(14) 0.42827(12) 0.0469(3) Uani 1 1 d . . .
C23 C 0.8186(3) 0.84549(15) 0.53365(15) 0.0595(4) Uani 1 1 d . . .
H23A H 0.6964 0.8468 0.5098 0.071 Uiso 1 1 calc R . .
H23B H 0.8921 0.8782 0.4791 0.071 Uiso 1 1 calc R . .
C24 C 0.9056(3) 0.92705(16) 0.66004(16) 0.0640(4) Uani 1 1 d . . .
H24A H 0.9186 1.0153 0.6655 0.096 Uiso 1 1 calc R . .
H24B H 1.0248 0.9230 0.6833 0.096 Uiso 1 1 calc R . .
H24C H 0.8295 0.8955 0.7128 0.096 Uiso 1 1 calc R . .
Cl1 Cl 1.12926(6) 0.72767(4) 0.21763(5) 0.07425(18) Uani 1 1 d . . .
O1 O 0.80764(17) 0.71540(10) 0.52957(9) 0.0587(3) Uani 1 1 d . . .
O2 O 0.62772(18) 0.64406(11) 0.34428(10) 0.0644(3) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.72(12) . . ?
C2 C1 C7 118.81(12) . . ?
C6 C1 C7 122.47(12) . . ?
C3 C2 C1 121.60(14) . . ?
C4 C3 C2 119.56(14) . . ?
C3 C4 C5 119.91(14) . . ?
C4 C5 C6 121.75(14) . . ?
C5 C6 C1 118.42(13) . . ?
C5 C6 C14 117.67(12) . . ?
C1 C6 C14 123.89(12) . . ?
C12 C7 C8 118.73(13) . . ?
C12 C7 C1 121.71(13) . . ?
C8 C7 C1 119.56(12) . . ?
C9 C8 C7 119.53(13) . . ?
C10 C9 C8 122.08(14) . . ?
C10 C9 Cl1 118.89(12) . . ?
C8 C9 Cl1 119.03(12) . . ?
C9 C10 C11 118.23(14) . . ?
C12 C11 C10 120.80(15) . . ?
C11 C12 C7 120.61(14) . . ?
C15 C14 C19 118.82(12) . . ?
C15 C14 C6 119.03(12) . . ?
C19 C14 C6 122.09(12) . . ?
C16 C15 C14 121.53(13) . . ?
C15 C16 C17 119.78(14) . . ?
C18 C17 C16 119.81(14) . . ?
C17 C18 C19 121.57(14) . . ?
C18 C19 C14 118.46(13) . . ?
C18 C19 C20 120.80(12) . . ?
C14 C19 C20 120.70(12) . . ?
C21 C20 C19 127.10(13) . . ?
C20 C21 C22 120.85(14) . . ?
O2 C22 O1 123.03(14) . . ?
O2 C22 C21 125.77(13) . . ?
O1 C22 C21 111.20(12) . . ?
O1 C23 C24 107.25(13) . . ?
C22 O1 C23 116.57(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3978(19) . ?
C1 C6 1.4061(19) . ?
C1 C7 1.4916(18) . ?
C2 C3 1.379(2) . ?
C3 C4 1.375(2) . ?
C4 C5 1.377(2) . ?
C5 C6 1.3954(19) . ?
C6 C14 1.4926(19) . ?
C7 C12 1.390(2) . ?
C7 C8 1.3927(19) . ?
C8 C9 1.380(2) . ?
C9 C10 1.375(2) . ?
C9 Cl1 1.7432(15) . ?
C10 C11 1.384(2) . ?
C11 C12 1.381(2) . ?
C14 C15 1.3928(19) . ?
C14 C19 1.4142(18) . ?
C15 C16 1.380(2) . ?
C16 C17 1.382(2) . ?
C17 C18 1.377(2) . ?
C18 C19 1.399(2) . ?
C19 C20 1.4632(19) . ?
C20 C21 1.322(2) . ?
C21 C22 1.467(2) . ?
C22 O2 1.2061(17) . ?
C22 O1 1.3346(17) . ?
C23 O1 1.4398(18) . ?
C23 C24 1.489(2) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.9(2) . . . . ?
C7 C1 C2 C3 178.35(13) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C1 -2.1(2) . . . . ?
C4 C5 C6 C14 176.41(14) . . . . ?
C2 C1 C6 C5 2.23(19) . . . . ?
C7 C1 C6 C5 -177.04(12) . . . . ?
C2 C1 C6 C14 -176.18(12) . . . . ?
C7 C1 C6 C14 4.5(2) . . . . ?
C2 C1 C7 C12 -129.63(14) . . . . ?
C6 C1 C7 C12 49.65(19) . . . . ?
C2 C1 C7 C8 49.42(18) . . . . ?
C6 C1 C7 C8 -131.31(14) . . . . ?
C12 C7 C8 C9 -1.6(2) . . . . ?
C1 C7 C8 C9 179.37(12) . . . . ?
C7 C8 C9 C10 1.1(2) . . . . ?
C7 C8 C9 Cl1 -178.37(10) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
Cl1 C9 C10 C11 179.31(12) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C11 C12 C7 -0.2(3) . . . . ?
C8 C7 C12 C11 1.1(2) . . . . ?
C1 C7 C12 C11 -179.80(14) . . . . ?
C5 C6 C14 C15 57.63(18) . . . . ?
C1 C6 C14 C15 -123.95(15) . . . . ?
C5 C6 C14 C19 -119.57(15) . . . . ?
C1 C6 C14 C19 58.85(19) . . . . ?
C19 C14 C15 C16 -0.7(2) . . . . ?
C6 C14 C15 C16 -177.95(13) . . . . ?
C14 C15 C16 C17 -0.9(2) . . . . ?
C15 C16 C17 C18 1.3(2) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
C17 C18 C19 C14 -1.4(2) . . . . ?
C17 C18 C19 C20 176.32(15) . . . . ?
C15 C14 C19 C18 1.8(2) . . . . ?
C6 C14 C19 C18 178.97(13) . . . . ?
C15 C14 C19 C20 -175.97(13) . . . . ?
C6 C14 C19 C20 1.2(2) . . . . ?
C18 C19 C20 C21 16.3(2) . . . . ?
C14 C19 C20 C21 -166.03(15) . . . . ?
C19 C20 C21 C22 179.39(14) . . . . ?
C20 C21 C22 O2 -1.5(3) . . . . ?
C20 C21 C22 O1 178.93(15) . . . . ?
O2 C22 O1 C23 -1.8(2) . . . . ?
C21 C22 O1 C23 177.83(14) . . . . ?
C24 C23 O1 C22 170.27(14) . . . . ?
